The semiconductor industry is currently considering the use of thin metal or metal containing films for a variety of applications. Many organometallic complexes have been evaluated as potential precursors for the formation of these thin films. Relevant art to this field includes:
Black, K., A. C. Jones, J. Bacsa, P. R. Chalker, P. A. Marshall, H. O. Davies, P. N. Heys, P. O'Brien, M. Afzaal, J. Raftery and G. W. Critchlow, “Investigation of new 2,5-dimethylpyrrolyl titanium alkylamide and alkoxide complexes as precursors for the liquid injection MOCVD of TiO2.” Chemical Vapor Deposition 16(1-3): 93-99 (2010).
Bradley, D. C. and M. H. Gitlitz, “Metallo-organic compounds containing metal-nitrogen bonds. Part V. Dialkylamidopyrrolyl- and dialkylamido-2,5-dimethyl-pyrrolyltitanium compounds” J. Chem. Soc., A FIELD Full Journal Title: Journal of the Chemical Society [Section] A: Inorganic, Physical, Theoretical(8): 1967-9 (1968).
Bynum, R. V., W. E. Hunter, R. D. Rogers and J. L. Atwood, “Pyrrolyl complexes of the early transition metals. 1. Synthesis and crystal structure of (η5-C5H5)2Ti(η1—NC4H4)2” Inorg. Chem. 19(8): 2368-74 (1980).
Bynum, R. V., H.-M. Zhang, R. D. Rogers and J. L. Atwood, “Pyrrolyl complexes of the early transition metals. 3. Synthesis and crystal structure of (η5C5H5)2Ti(η1—NC4H2Me2)2 and (η5C5H5)2Zr(η1—NC4H2Me2)2” Can. J. Chem. 64: 1304. (1986).
WO09155507A and WO09155520A1 by Davies, H. O., P. N. Heys, A. Kingsley and R. Odedra.
Dias, A. R., A. P. Ferreira and L. F. Veiros, “Bonding Geometry of Pyrrolyl in Zirconium Complexes: Fluxionality between σ and π Coordination.” Organometallics 22(24): 5114-5125 (2003).
Dias, A. R., A. M. Galvão, A. C. Galvão and M. S. Salema, “Synthesis, characterisation, crystal structure, reactivity and bonding in titanium complexes containing 2,3,4,5-tetramethylpyrrolyl.” Journal of the Chemical Society—Dalton Transactions 1055-1061 (1997).
Ferreira da Silva, J. L. and A. C. Galvão, Ferreira, A. P., Galvão, A. M., Dias, A. R., Gomes, P. T., Salema, M. S., “Effect of ancillary ligands in the hapticity of the pyrrolyl ligand in [Ti(pyrrolyl)(NMe2)xCl3-x] (x=0, 1, 2, 3) complexes.” Journal of Organometallic Chemistry 695(10-11): 1533-1540 (2010).
DE4120344A by Heinen, R. and T. Kruck.
WO2009086263 by Heys, P. N. and H. O. Davies.
Huang, J. H., P. C. Kuo, G. H. Lee and S. M. Peng, Synthesis and structure characterization of 2-(dimethylaminomethyl)pyrrolate and 2,5-bis(dimethylaminomethyl)pyrrolate zirconium complexes” Journal of the Chinese Chemical Society 47(6): 1191-1195 (2000).
Kuhn, N., S. Stubenrauch, R. Boese and D. Bläser, “XVI. (2,5-C4tBu2RH2N)MCl3 (M=Ti, Zr, Hf; R═H, SiMe3)—Azacyclopentadienyl-Komplexe der Gruppe 4-Metalle.” Journal of Organometallic Chemistry 440(3): 289-296 (1992).
Li, Y., A. Turnas, J. T. Ciszewski and A. L. Odom, “Group-4 η1-pyrrolyl complexes incorporating N,N-di(pyrrolyl-α-methyl)-N-methylamine.” Inorganic Chemistry 41(24): 6298-6306 (2002).
U.S. Pat. No. 7,332,618 by Meiere, S. H.
US20080081922A1 by Meiere, S. H., J. D. Peck, R. F. Spohn and D. M. Thompson.
U.S. Pat. No. 5,300,321A by Nakano, T. and T. Ohta.
Swartz II, D. L. and A. L. Odom in “Synthesis, Structure, and Hydroamination Kinetics of (2,2′-Diaryldipyrrolylmethane)- and Bis(2-arylpyrrolyl)titanium Complexes.” Organometallics 25(26): 6125-6133 (2006).
Tanski, J. M. and G. Parkin, “Synthesis and structures of zirconium-pyrrolyl complexes: Computational analysis of the factors that influence the coordination modes of pyrrolyl ligands.” Organometallics 21(4): 587-589 (2002).
A need still exists in the industry for developing new compounds and for exploring their potential as chemical vapor deposition (CVD) and atomic layer deposition(ALD) precursors for film depositions.